Mac Mail vs. Microsoft Outlook: The dirty truth

Erik Eckel takes a look at how Mac Mail performs next to Outlook for Mac. Which do you prefer and why?

Sometimes, I find myself wanting to become an Apple fanboy. It would be easier, after all,
within the hectic, ever-changing IT industry to just know I can trust what the
manufacturer tells me. But years of technology consulting have taught me that vendors are evil.

Yes, it’s true. I’m sorry you had to read it here. But that's the way it is in the real world, where the consulting firm I operate
services hundreds of different commercial businesses and organizations. Vendors
will promise you the world and assure you its mail client (or other product) is
the best. However, your experience may differ.

Even before I began offering IT services to others, family
and friends purchasing new Macs would frequently ask which email client is the best
on OS X. I’ve always been partial to OS X Mail, which should
make Apple developers happy. They’ve earned the accolade. The app is integrated
within the OS, loads quickly, boasts a basic but attractive interface, possesses
clean and well-laid elements, and proves to be easily navigable. Composing messages,
replying to email, and sorting the inbox are painless tasks. Creating rules or
email signatures within Mail doesn’t induce knee-knocking anxiety, the way doing
so might in, say, Microsoft Outlook. Mail is simple and not that
complicated, and the resulting lack of complexity makes it more approachable.

Microsoft’s older Entourage
applications, of course, earned little popularity. Rightfully so. Many Entourage
users complained of database corruption and slow performance. Microsoft wisely replaced
Entourage with Outlook. With
Outlook for Mac 2011’s release, I was hopeful that a new standard was in hand. But
I’ve been disappointed. Outlook takes longer to open (my scientifically
invalid, non-double-blind testing shows Outlook requires 23 seconds to open,
whereas Mail requires only five), regularly encounters synchronization delays, and often simply doesn’t update my Exchange mailbox with changes as accurately
or rapidly as does Mail, at least in my experience.

Ultimately, I use both Mail and Outlook for Mac, if for no
other reason than to stay current with both platforms. I’ve configured the Macs
in my home and business to connect to POP3, IMAP, and Exchange accounts, too,
and I access mail, contacts, and calendars using Outlook and OS X’s built-in
Mail, Contacts, and Calendar. Apple’s unending efforts to improve Mail, including
message integration within Notification Center, iCloud reliability improvements, and Conversation views are encouraging and continue to make Mail a favorite
application.

However, Mail isn’t perfect.

Outlook, ultimately, gains an edge due to the clean manner
in which it successfully integrates contacts and calendaring. Opening shared
calendars, in particular, is easier within Outlook, in my opinion, than within
Calendar. And Outlook consistently displays HTML email messages, specifically
marketing messages that I’ve requested to receive, properly.

Mail stumbles on that front. Marketing messages that are sent by
large, well-known firms you would recognize (ThinkGeek, Barnes & Noble, and
NPR are a few examples) and may also receive within your inbox, regularly
fail to format properly within Mail. That’s frustrating.

So, it’s a tradeoff. If you want the ease of use and generally
acceptable performance Mail provides, you can save hundreds of dollars per Mac
leveraging Mail instead of Outlook. But if you operate within an enterprise
environment, you may well not have time for workarounds and simply find Outlook
the best fit. But if you or your users also need Word, Excel, and/or PowerPoint,
Outlook’s almost certainly going to be included with the license your
organization purchases, and firing up Outlook becomes a no-brainer. Just be
sure to give Outlook time to open and then sync changes with Exchange before
exiting the program.

Which do you prefer: Mac Mail or Outlook for Mac? Share your opinion in the discussion thread below.

Excelent review... Thank you you resolve my doubts... im a new mac user... and leaving behind outlook is one of the most hard thinks to do.... naaah... just kidding, outlook always has been a delayed plataform... Im glad Mac mail works so efficently. it also has easly commands and the facility for it use is amazing, even a 3 year old child can use it...

Again thank you for your review... it really help, because i was wondering if i should go back to outlook but i was worried to take a bad chooise but you make it easy... A+++

I would love to use the new Outlook 2015 for the MAC, but I can not send emails. I have gone through what threads are out there but nothing works. I should say that Outlook did work for the first 5 days and then just stopped working (sending emails, receiving is fine). Anyone else have this problem?

One of the issues I am having using both Outlook and Mac Mail on my Mac is that there are two users on my Mac. I prefer Mac Mail, but my spouse prefers Outlook. There is some sort of conflict between these apps because when my spouse uses Outlook to send an email, Mac Mail automatically opens. Although this is a not a major issue, I prefer to keep my emails private, and having my inbox pop open whenever my spouse uses Outlook to send mail annoys both of us. I wish this could be fixed.

I have always used Outlook (IMAP) on my Windows PC but just got my first MacBook Pro. I downloaded Office 2011 and everything was working great for the past week. Suddenly, I'm no longer able to open Outlook. Everything else works great. I've uninstalled and reinstalled Office 3 times this morning already with no change. Outlook will not open. I am looking into using Mac Mail but am not sure I'll have all the bells and whistles that are important for me. Right now, I'm just extremely frustrated about Outlook. Things on this Mac shouldn't be this difficult! Anyone else have problems with Outlook simply quit working and refuse to open? If so, what did you do to remedy it?

I have Hotmail configured using IMAP within Mac Mail and it's great 99% of the time, I much prefer it to using the browser to load up a webpage and login. The only issue is that sometimes Mac Mail sends the same email multiple times! Often I get emails from people asking to please stop sending them repeated emails. I had to delete the profile in "accounts" and re-create to fix the issue. No biggy.

I preferred Mail for several years. Mavericks has changed that. It's finally Gmail-friendly with 10.9.2, but Mail on my iMac still taxes cpu like a madman, fails to display approximately 50% of new messages in the inbox unless I leave/return to the inbox, and resurrects many previously-deleted emails.

Outlook -- Is there a way to turn off those insidious tooltips? They actually cover up what I'm attempting to read. Search Google to see how annoying this is in Mac and Windows versions. Microsoft has had YEARS to fix this obvious oversight -- at least give us the option of turning tooltips off. That's problem #1 of a long list. Outlook does a few things extremely well. You can move an email to any folder in any account just as quickly as you can in Mail with the awesome Mail Act-On utility. Finding and opening that folder -- different story. It's difficult to believe that anyone in Redmond actually uses Outlook 2011.

My most reliable email application is Mail iOS. I have tried numerous Mac applications since getting Mavericks. Like Outlook, most do a few things well, but have enough problems to make the app unreliable, annoying, or both. Anyone who creates a reliable, easy-to-use email application for Mac will be quite rich very quickly.

I was a bit of a power user in Outlook for PC before switching to a Mac. The 1st drawback of OL for Mac was the font incompatibility - perfect-looking messages show up in the recipient's mailbox looking like they were written by a 3rd grader. But that's a platform issue rather than an Outlook issue. 2nd drawback was that the functionality in terms of formatting emails isn't as broad in the Mac version and I missed that ability.

The kicker, and why I'm using Mail even though I preferred Outlook was that Outlook crashed. Badly. I lost about 14K messages, which had all been organized in folders. I had to reinstall Outlook and re-download everything. In fact, I had to reinstall my entire OS. Then it happened a few more times. So, once it was corrupt on my MacBook I spent countless hours trying to fix it with tech support and then gave up. I have since migrated to using IMAP, which of course would have helped but it was a very bad experience. I also learned that you need to back up your Outlook outside of time capsule, which won't properly restore outlook for Mac.

Recently switched to a Mac from a Windows 7/Outlook 2010 environment. Company uses enterprise Gmail, so Outlook was using the Google App Sync. I was relatively happy with Outlook in that environment, but when switching to a Mac I really wanted to avoid running a Windows VM if at all possible, and stick to a pure Mac environment.

Setting up Mac Mail 7.2 with multiple Gmail accounts was relatively easy, although I wish I could have specified how much data I wanted to download locally. I am a pack rat so it took a while to download all of my email, and I'm sure a significant amount of space.

I had to make some adjustments to the SMTP servers after the fact, like changing the port numbers and my user name. The wizard didn't set that up properly for me. However, once it started working I have been extremely happy with the Mail application. Especially helpful is the Junk mail feature. Getting that to work in Outlook in a Gmail environment is nearly impossible. In comparison, I am easily able to filter Junk email with the Mail 7.2 application.

About the only thing I am missing is a 3rd party WebEx plug-in for the Calendar application to automatically create WebEx meetings as part of my calendar invites.

So far I am loving Mail 7.2 and my Mac, especially the Spotlight search which searches EVERYTHING, including Mail. When Microsoft stopped including emails in their global search (Windows 8/Office 2013) I stopped upgrading my OS and Office from Windows 7 and Office 2010. Now that I'm on a Mac again after about 20 years of being away I'm loving it.

Outlook does not support iCloud Calendars and Contacts - a big negative for Outlook (since I use iCloud). On the other hand, Mail does has some glitches with Exchange calendar invites, exchange mail syncing, and rules.

I've flip-flopped between them many times, but I am ultimately stuck with Outlook because my office is on Exchange and the items in the pro list supersede the Mail pros. I wish I could get all the Outlook features I like in Mail!

However, apple mail is giant player for the functioning of speedy & reliable mail service but Outlook 2011 is well know for its enriched features. Most of guys are loved Outlook 2011 for ease functioning. In case, anyone is interested to migrate from apple mail to Outlook 2011 then easily can be done through Microsoft certified stellar apple mail to Outlook 2011 converter available.

I've been a jumping jack for quite a while and I have had the oppty to use all the three....MS Outlook, Thunderbird ,OWA and OSX Mail .

I definitely would vote for MS Outlook.

Let me share the main issues using OWA, Thunderbird, Mail etc :

1. The fonts and formatting is a pain in the ...! I format it so carefully as it is all for business and I see that my font varies from time to time .It never had the consistency . Mail default font is Helvitica and most of the users may not have that and it shows in Times New Roman, which definitely is old fashioned and looks weird with the signature being in some xyz font.

2.Mail receiving and forwarding in Mail and thunderbird is little time consuming and you wouldn't know if the attachment is there or not. In outlook and owa you can see that there are attachments attached under the subject box.

3.Sending calendar invites is little difficult in owa, mail and thunderbird. In Gmail and MS outlook you have the insert option/invite option on top which is very easy.

will be thankful if any of the mail users can share their best experiences in using mail and tips to make my MacBook mail experience better.

My answer is- NEITHER. I moved to the Mac platform for much the same reason as you- to move to a single-vendor, controlled platform, and for the most part it's been...OK. I guess I was hoping for the heavens to open up and bestow the wisdom of the late Mr. Jobs upon me. Still waiting for that.

However- the mail experience has been horrific on both fronts. My firm uses Exchange, recently moved to Office365 (the same thing but 'out there'), for a remote worker there's no effective difference. Do you want to know what I need to do to be "mail functional"? I have to have Parallels and use MS Outlook 2013 in a windows VM, or, if I'm online, I find it even easier to RDP to a VDI workstation in my office and run Outlook there. Outlook 2011 is awful and a resource hog. It's also not fully baked in with Exchange 2010/2013. OSX Mail is a clean app, but definitely made for the gmails/imap/pop accounts of the world, NOT enterprise messaging apps.

I've even found OWA in safari or chrome to work better than the two. I'd advise Microsoft to take their OWA app for iOS and port it to OSX and I think I'd live in that! (Hey, M$, you listening?? Do THAT.)

Having used Entourage for many years, I recently purchased a new laptop and rather than purchase Outlook was pursuaded to give Mail a go.
I'm not getting on at all well with it. One of the main problems I have
is when sending image attachments it seems to randomly embed the image
into the email despite checking the box for windows friendly
attachments. Has anyone found a way around this problem?

Quote: "So, it’s a tradeoff. If you want the ease of use and generally acceptable performance Mail provides, you can save hundreds of dollars per Mac leveraging Mail instead of Outlook. But if you operate within an enterprise environment, you may well not have time for workarounds and simply find Outlook the best fit."

This sums up my experience as well. Although it is possible to cobble together a workplace solution from Apple-developed applications, they are nothing like the connectivity that Microsoft products provide out-of-the-box for business use.

For those whose core applications require running another OS (Mac OS or Linux, for examples), I have found running Office in a "winebottle" created by CrossOver, for example, to be an effective and easy to maintain solution.

I make extensive use of Outlook Tasks functionality (in Windows). I have not found anything in the Apple (or Android) ecosystem that comes close in functionality and lets me share task info with my windows machine. For that reason, it's Outlook in Windows for me.

I find myself in Thunderbird more than any other mail client. My big issue is that I develop cross platform apps and find myself mostly on some flavor of linux, alot on Macs and occasionally on Windows. Tbird behaves the same. I use imap on my servers and the University uses Exchange.

I don't really disagree with anything the author said and Mail and Outlook do work but only on some of the systems I work with.

I am speaking from an experiential point of view in having had to provide Tech Support for many email issues with MACS, IPads, & IPhones for the last few years so I am well acquainted with the downside of email clients on Apple devices as well as windows based devices. I freely admit I have always been more of a Windows guy than an OSX guy and have a built in prejudice favoring Outlook. Having said that I would like to make a few observations that may be of interest. One is my surprise at the large percentage of die hard MAC users that actually preferred Outlook to OSX Mail that I encountered while providing tech support. The main problem with Apple Mail or Mac Mail is as with any client there are times one is forced to remove an account and reinstall it to correct problems and when you do this you lose everything. Any saved emails are history. While that can happen with Outlook usually if you remove an account & reinstall it your saved emails are still there. The other big negative I encountered was when Apple came out wit the iOS6 upgrade it pretty much bricked everyone's email accounts on their I-Phones and I Pads and the only solution we ever found was to remove the account and re-enter it on the device. Most small businesses have saved emails they do not want to lose but if they weren't archived on the server they were just SOL.

Everytime I try to stop using Apple Mail I keep finding my way back to
it. Thunderbird, Postbox, Outlook, they all have their pros and cons.
But I'm a mail purist. And Mail.app gives me the least hardship with a
task I have to do all day and night. I don't want a lot of integration
with other things when it comes to a mail client BTW - so I may not be
your best person to ask :)